My husband and I ventured to Old Town for a few days in September to savor our last trip as a family of two before we welcome our first little one in December. We booked cheap flights through Allegiant directly into the Keys during off season — and while I wouldn’t recommend visiting in September (so, so hot especially at six months pregnant😅), it was less crowded and we had most places almost entirely to ourselves. Keep in mind we weren’t visiting for the bar scene, because, well, the baby. I’ve also spent most of the year traveling abroad so I purposefully didn’t plan a trip with a detailed itinerary. We just simply hung out and explored — but I think we found some gems worth sharing with you!
Where We Stayed
I don’t know much about other parts of the Keys, but our Airbnb in Old Town was perfectly located for a quick visit, especially if you’re looking to get a taste of the culture. We were 10 minutes from the airport, a block off of Duval (the main street in town, but it wasn’t loud at all), and we could walk everywhere we needed to be (including the distance from each side of the island). The house was super clean, had a private hot tub, and access to two semi-private pools (we never had a visitor the entire time we were there). Plus, it was more affordable than the resorts. I’d definitely stay again.
Check out the Center Court Historic Cottages on Airbnb — basically anything hosted by Naomi is all in one area with use of the same pools and other shared spaces. We actually booked Harrison’s Hideaway, but were upgraded to Family House due to a maintenance issue in the original location.


A surprise bonus? The yummiest Cuban food only a few feet away (see below)!
Beaches
Everyone mentioned Key West “not being a beach town,” but don’t let that scare you. While I would agree it’s more of a party and watersports scene, you can absolutely visit beaches and lounge for the day. We thoroughly enjoyed both beaches we visited. In general, they remind me of European beaches — more natural (which means rockier and smaller). You also pay a pretty price for chairs and umbrellas on the public beaches. If you’re traveling on a budget, you can take your towels and plop in the sand, but this mama wasn’t doing it.
Smathers Beach was our top pick. It’s big (and wasn’t crowded because of the off season). There’s a huge sand bar 30 yards out in the ocean, which makes it the perfect place to relax. From the shoreline, you can see the changes in the water colors. We would wade out to the sand bar and then lay sit in the shallow water for hours. We saw a few jellyfish, a stingray, and tropical fish! If you plan on spending the day like we did, there are restrooms on the beach but food was a little hard to come by. Apparently food trucks line the street during the busy season, but if you’re braving off-season like us, head across the street to Margaritaville Beach House Hotel for good food at their outdoor restaurant. Just make sure you have a shirt and shoes.




Fort Zachary was also a good spot. It’s a state park so you pay a few bucks to enter, but the beach is really nice. We didn’t like the water as much because there wasn’t a sandbar. There was a tiki bar and restrooms on the beach which were convenient (but the food was pricey for the quality IMO).





Where to Eat (Hint: Anywhere With Cuban Food)
The first thing we did was ask two locals their favorite place for authentic Cuban — and I’m so glad we did! Both of them mentioned El Siboney so we got it the first night we were there and it didn’t disappoint. Try the Roast Pork or Ropa Vieja (beef with a tomato sauce) because they’re both delicious:


We were also lucky to stumble upon Key West Cuban Coffee two doors down from our Airbnb. It had THE BEST empanadas I’ve had to date, the biggest rice bowls, and yummy everything, including the classic Cuban sandwich pictured below. We went back twice and wish we would’ve discovered it sooner. Alex also liked their Cuban espresso.




For dinner, we stumbled across Onlywood by accident — and in classic Alex and Katelyn travel tradition — we went back twice. I know, I know … there are so many different places to try, but their pizza sold us on night one.







And finally, what’s vacay without sugar? I hope I never have to find out. You have to go to Mattheessans and get the 1/2 pound cookies. We spent $15 bucks on the Cookie Monster sundae and crushed it. The crunchy turtle ice cream was soo good, and Alex loved the key lime pie.
We also grabbed Flamingo Crossing Ice Cream and it was equally delicious. The Oreo was packed with cookies, and it was super creamy. Alex went for the key lime pie flavor (again).



Catch the Sunsets
I booked one thing — and if you know me, you know it was a boat cruise. I’m happiest on the water! I definitely recommend the 2-hour Sunset Sail with Live Music through Sebago Watersports. I love live music so it was definitely a plus — and it’s open bar with snacks all night (the shrimp cocktail hit the spot). I booked through GetYourGuide.




You also need to catch the sunset from Sunset Pier. There was live music the night we were there, good drinks, and just the best view.





We really did have the best four days together alone in each other’s company. We’re often traveling with friends or family, so the rare moments alone were super special. We decided on our next visit we’ll fly into Miami, rent a car, and drive through the Keys to switch it up — and we definitely want to take a sea plane to the Dry Tortugas + Alex would die for a deep sea fishing trip. But that’s all for next time…
We ended the trip by buying a sweet baby book about roosters (they’re everywhere in Key West) and a onesie to remember our babymoon. We want our little one to know they made the journey with us 🙂


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